It’s a good bet that the mysterious, New York-trained Harry Sonntag, nicknamed Key Largo’s Hermit Artist, never met any of the 26 mostly self-taught, African-American painters from Fort Pierce who became known decades later as the Highwaymen.

But for the first time, their work will be displayed together during a two-month show described as “Two Original Collections — One Unique Exhibit.” It opened this week at the Florida Keys History & Discovery Center at the Islander Resort in Islamorada.

The exhibit showcases more than 70 pieces — 15 by Sonntag and the remainder by nine of the Highwaymen, including the only Highwaywoman, Mary Ann Carroll.

“It was a perfect match: same genre, same time period [1950s to ’80s],” said Jill Miranda Baker, the center’s executive director.

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The exhibit takes the viewer back to Old Florida before all the development, with oil paintings and watercolors that show romanticized post-card images of the peninsula state and its natural beauty.

“My family came from Jacksonville, and we owned orange groves and turpentine stills,” said Anne Baxter, who inherited from her mother Highwaymen paintings that are in the exhibit. “These paintings evoke an appreciation of Florida landscapes, the way Florida is, and why people came here: the Spanish moss; the cypress trees; the lovely waters.”

The exhibit also showcases the diverse artists’ fascinating histories. Sonntag’s “life’s works” were thought to be destroyed in a fire at his Key Largo Art Gallery in 1955. But many turned up nearly four decades later in a garbage bag collecting dust in a storage unit in Kissimmee.

The Highwaymen, who wanted to avoid the menial work at packinghouses and citrus groves during the time of segregation, created a cottage industry in which they quickly painted landscapes and then sold the art for cheap — often before it had time to dry.

Gary Monroe, whose 2001 book The Highwaymen: Florida’s African-American Landscape Painters sparked a cultural phenomenon, opened the exhibit Wednesday evening with a talk about the painters — whose works have been sold at yard sales for $3 and purchased by one collector for $40,000.

While Harold Newton was perhaps the best painter, Monroe says it was Alfred Hair who was the progenitor of the Highwaymen story. Hair was the only one who was taught to paint, by successful white landscape artist A.E. Bean Backus.

Hair wanted to become a millionaire by age 35, but being a realist he knew that as an 18-year-old black man in the South, he could not command the $250 to $300 per painting that Bean did.

So Hair painted fast, figuring if he could paint 10 works in the time it took Backus to paint one he could sell his for a 10th of the price, or about $25.

“If he hustled them quickly, he’d make the same amount of money,” Monroe said. “I’ve been to his house and saw the back patio he referred to as his studio. He’d put up 10 boards at a time and whip right through them.”

That style of fast painting, according to Monroe’s interpretation, is what made the Highwaymen’s art special.

“Hair and his cohorts unintentionally corrupted the cherished concerns of classical romantic landscape painting,” Monroe said. “In other words, they screwed up the formula. But what happened, because they painted so quickly without great detail but with great exuberance, they arrived at a different kind of landscape painting: one less definitive, less narrative but way more suggestive. It’s almost like it needed to be completed in the viewer’s eyes.”

Monroe has gone on to write three more books about the Highwaymen, including Mary Ann Carroll: First Lady of the Highwaymen, which will be published in August by University Press of Florida.

Nobody knows how many Highwaymen paintings are in existence — especially with some of the surviving artists having returned to painting. High estimates put the number at 250,000. Monroe thinks it is closer to 125,000.

For this Highwaymen exhibit, Lisa Stone of Lisa Stone Arts chose works from four of her private collector clients: Monroe, Scott Schlesinger, Earl Powell and the late Gray Brewer. Brewer was believed to be the first collector of Highwayman art, starting in 1958.

Schlesinger said his father bought Highwaymen paintings directly from the artists out of their car trunks. In 1998, he began his own collection; he has lost count of how big it has become.

“They make people feel good, and they make people feel happy,” he said. “The ocean scenes. The palm trees. The backcountry with old pine and palmetto wood. Beautiful sunrises and sunsets. Bubblegum pink skies. Some people say they may look cartoonish, but you drive around Florida and you’ll see that exact sunset and say: ‘Wow, that looks like a Harold Newton painting I have.’ ”

When word got out in the Upper Keys about the exhibit, local collectors literally came out of the woodwork to offer up their Highwaymen paintings for the exhibit. “We had to turn people down because we ran out of room,” said Brad Bertelli, curator at the discovery center.

Attorney Cheryl Culberson loaned an Ellis Buckner painting she had bought from him for around $275 in the early 1980s at a seafood festival in Islamorada — and that had survived Hurricane Andrew. Longtime Everglades advocate Mary Barley loaned her Harold Newton painting that her late husband bought around Titusville in the late 1950s or early 1960s.

Mark Kohl loaned three James Gibson paintings that had decorated his offices when he was the Monroe County state attorney. His father, Don Kohl, had bought them around 40 years ago. While the going price was $25, Don Kohl told his son: “I might have given him $30.”

Monroe explained how the Highwaymen made their own frames out of door and window trim they bought at a hardware store — not that they stole, as was once written. They painted them and put on streaks of gold to make them look like antiques.

“See, there’s the gold,” Kohl said, pointing to a frame. “I never knew that before.”

The Sonntag collection

Also in the crowd Wednesday night was Chuck Faulkner, who owns the entire Harry Sonntag collection. He will give a talk May 1 at the discovery center.

Sonntag opened the Florida Keys Art Gallery, the first in the Keys, in 1951 in an abandoned lime packing plant. But when it burned down in 1955, he disappeared. That might have been the end of his known story if not for Faulkner and his collectibles partner Frank McNall.

In 1992, McNall just happened to come across an elderly woman cleaning out a storage unit. He bought a dirty garbage bag full of watercolors and press clippings “for a very good price.” Faulkner got part ownership of the bag after convincing McNall that he should get the bag out of the back of his truck before it rained, which it did 30 minutes later.

The bag had been in storage since 1960, when a Kissimmee couple vacationing in St. Thomas found it under the bed of a rooming house and brought it back with them. The bag contained 165 paintings, including some chronicaling Sonntag’s earlier life in New York as well as many of the Florida Keys — all works that supposedly were destroyed in the Key Largo fire.

Sonntag died in St. Petersburg in 1991, and not much else is known about him after he left the Keys. What is known is he was born in 1900 in Astoria, N.Y., and at age 16 began to study painting at the Pratt Institute of Art. In the early 1940s he moved to Manhattan and worked in a private studio, where a fire a few years later destroyed all his paintings.

Sonntag spent the next few years wandering around the country before settling in Rock Harbor, part of Key Largo. He lived in a shack built from driftwood and tarpaper, where he painted island landscapes and scenes of fishermen and marinas. In 1951, during tourist season, he opened the Key Largo Art Gallery.

Those who knew Sonntag when he lived in the Keys said in a 1998 local newspaper article that he literally was a starving artist who would boil seaweed to eat rather than “sacrifice the value of his soul as seen through his artwork.” His watercolors sold for $55 to $65, steep for the time, and there was no negotiation, Bertelli said.

A 1952 article in the Miami Daily News put the gallery on the map. Sontagg told the writer: “Art is the universal language and my desire is to bring beauty to the multitude, so people may realize how lovely is this world.”

Among the Sonntag paintings Faulkner has brought to the current exhibit is one of an open air Key West art show. Faulkner found an old newspaper article that mentions young boys trying to spill the water Faulkner was using for his watercolors at the event.

“That collection has been like a child to me,” said Faulkner, who has kept most of it intact over the years. “But now it’s time to move out of the house.”

Faulkner, 57, would like to sell the collection to someone who would want it to be given to a museum. “I’m not really sure what it’s worth,” he said. “I used to tell people about $2 million.”